US20170362508A1 - Polymerizable compound and optically anisotropic body - Google Patents

Polymerizable compound and optically anisotropic body Download PDF

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US20170362508A1
US20170362508A1 US15/542,537 US201615542537A US2017362508A1 US 20170362508 A1 US20170362508 A1 US 20170362508A1 US 201615542537 A US201615542537 A US 201615542537A US 2017362508 A1 US2017362508 A1 US 2017362508A1
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Masahiro Horiguchi
Akihiro Koiso
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DIC Corp
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Definitions

  • the present invention relates to a compound having a polymerizable group, a polymerizable composition containing the compound, a polymerizable liquid crystal composition, and an optically anisotropic body using the polymerizable liquid crystal composition.
  • a polymer having uniform alignment can be produced by aligning, in a liquid crystal state, a polymerizable composition containing a polymerizable compound, and then polymerizing the composition.
  • a polymer can be used for a polarization plate, a retardation plate, and the like necessary for displays.
  • a polymerizable composition containing two or more types of polymerizable compounds is used for satisfying the required optical characteristics, polymerization rate, solubility, melting point, glass transition temperature, polymer transparency, mechanical strength, surface hardness, heat resistance, and light resistance.
  • the polymerizable compounds used are required to impart good physical properties to the polymerizable composition without adversely affecting other characteristics.
  • Liquid crystal displays used outdoors or in a place exposed to a high temperature are required to have higher-reliability than usual liquid crystal displays.
  • in-vehicle products, and the like particularly high heat resistance and light resistance are required.
  • Various polymerizable compounds have been reported for applications to retardation films for improving viewing angles of liquid crystal displays.
  • the films produced by using the polymerizable compounds may be decreased in retardation or may be discolored (Patent Literature 1 and 2).
  • the films which may be decreased in retardation or may be discolored are used in, for example, liquid crystal displays of a mobile product, an in-vehicle product, and the like, brightness unevenness in screens or unnatural colors occur due to long-term use, thereby causing the problem of significantly decreasing the quality of the products. Therefore, there has been demand for development of a polymerizable compound capable of solving the problem.
  • a problem to be solved by the present invention is to provide a polymerizable compound and a polymerizable composition which cause little decrease in retardation and discoloration when a film-shaped polymer produced by polymerization is irradiated with ultraviolet/visible light for a long time at high temperature.
  • a further problems is to provide a polymer produced by polymerizing the polymerizable composition and an optically anisotropic body using the polymer.
  • the present invention provides a polymerizable liquid crystal compound having an absorption maximum wavelength ⁇ omax at 320 nm to 420 nm in an in-plane direction perpendicular to an alignment direction when aligned on a horizontally-aligned substrate, and also provides a polymerizable composition containing the compound, a polymerizable liquid crystal composition, a polymer produced by polymerizing the polymerizable liquid crystal composition, and an optically anisotropic body using the polymer.
  • a compound of the present invention causes little decrease in adhesion and little discoloration when a film-shaped polymer produced by adding to a polymerizable composition and polymerizing the composition is irradiated with ultraviolet/visible light for a long time at high temperature, and thus the compound is useful as a component of a polymerizable composition.
  • an optically anisotropic body using a polymerizable liquid crystal composition containing the compound of the present invention is useful for applications to optical materials such as a retardation film and the like.
  • liquid crystalline compound is intended to represent a compound having a mesogenic skeleton and the compound by itself may not have liquid crystallinity.
  • the present invention provides a polymerizable liquid crystal compound in which when aligned on a horizontally-aligned substrate, an absorption maximum wavelength ⁇ omax in an in-plane direction perpendicular to an alignment direction lies at 320 nm to 420 nm, and also provides a polymerizable composition containing the compound, a polymerizable liquid crystal composition, a polymer produced by polymerizing the polymerizable liquid crystal composition, and an optically anisotropic body using the polymer.
  • the absorption maximum wavelength ⁇ omax in an in-plane direction perpendicular to an alignment direction can be measured as follows. Measurement is performed by using a spectrophotometer, and an absorption spectrum is measured by disposing a film to be evaluated and a polarization plate on the detector-side surface of the film so that the alignment direction of the film is perpendicular to the polarization direction of the polarization plate (refer to a drawing).
  • a compound to be evaluated may be applied alone on a substrate, may be diluted with a solvent and applied, or may be mixed with another component and applied.
  • the wavelength showing the maximum value among the plurality of absorption maximums is defined as ⁇ omax.
  • absorbance Ae in the direction parallel to the alignment direction and absorbance Ao in the in-plane direction perpendicular to the alignment direction preferably satisfy a formula (Formula I) below.
  • the absorbance Ao at the wavelength ⁇ omax in the in-plane direction perpendicular to the alignment direction is determined by the method for measuring ⁇ omax described above.
  • the absorbance Ae in the direction parallel to the alignment direction can be determined by measuring an absorption spectrum by disposing a film to be evaluated and a polarization plate on the detector-side surface of the film so that the alignment direction of the film is parallel to the polarization direction of the polarization plate (refer to the drawing).
  • P 1 represents a polymerizable group
  • S 1 represents a spacer group or a single bond, and when a plurality of S 1 are present, they may be the same or different
  • X 1 represents —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH ⁇ CH—COO—, —CH ⁇ CH—OCO—, —COO—CH ⁇ CH—, —OCO—CH ⁇ CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2
  • P 1 represents a polymerizable group and preferably represents a group selected from formula (P-1) to formula (P-20) below.
  • These polymerizable groups are polymerized by radical polymerization, radical addition polymerization, cationic polymerization, and anionic polymerization.
  • the formula (P-1), the formula (P-2), the formula (P-3), the formula (P-4), the formula (P-5), the formula (P-7), the formula (P-11), the formula (P-13), the formula (P-15) or the formula (P-18) is preferred, the formula (P-1), the formula (P-2), the formula (P-7), the formula (P-11), or the formula (P-13) is more preferred, the formula (P-1), the formula (P-2), or the formula (P-3) is even more preferred, and the formula (P-1) or the formula (P-2) is particularly preferred.
  • S 1 represents a spacer group or a single bond, and when a plurality of S 1 are present, they may be the same or different. Also, S 1 preferably represents as the spacer group an alkylene group having 1 to 20 carbon atoms in which one —CH 2 — or two or more unadjacent —CH 2 — may be each independently substituted by —O—, —COO—, —OCO—, —OCO—O—, —CO—NH—, —NH—CO—, —CH ⁇ CH—, or —C ⁇ C—.
  • a plurality of S 1 When a plurality of S 1 are present from the viewpoint of easy availability of raw materials and easy synthesis, they may be the same or different and more preferably each independently represent an alkylene group having 1 to 10 carbon atoms, in which one —CH 2 — or two or more unadjacent —CH 2 — may be each independently substituted by —O—, —COO—, or —OCO—, or a single bond, and even more preferably represent an alkylene group having 1 to 10 carbon atoms or a single bond. When a plurality of S 1 are present, they may be the same or different and particularly preferably each independently represent an alkylene group having 1 to 8 carbon atoms.
  • X 1 when a plurality of X 1 are present, they may be the same or different and preferably each independently represent —O—, —S—, —OCH 2 —, —CH 2 O—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, or a single bond, and even more preferably represent —O—, —OCH 2 —, —CH 2 O—, —COO—, —OCO—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, or a single bond, and even more preferably represent
  • k represents an integer of 0 to 8
  • k preferably represents an integer of 0 to 4, more preferably represents an integer of 0 to 3, even more preferably represents an integer of 0 to 2, and particularly preferably represents 1.
  • a 11 and A 12 preferably each independently represent a 1,4-phenylene group, a 1,4-cyclohexylene group, or a naphthalene-2,6-diyl group, which may be unsubstituted or substituted by one or more L, more preferably each independently represent a group selected from formula (A-1) to formula (A-11) below,
  • Z 11 and Z 12 preferably each independently represent a single bond, —OCH 2 —, —CH 2 O—, —COO—, —OCO—, —CF 2 O—, —OCF 2 —, —CH 2 CH 2 —, —CF 2 CF 2 —, —CH ⁇ CH—COO—, —CH ⁇ CH—OCO—, —COO—CH ⁇ CH—, —OCO—CH ⁇ CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —CH ⁇ CH—, —CF ⁇ CF—, —C ⁇ C—, or a single bond, more preferably each independently represent —OCH 2 —, —CH 2 O—, —CH 2 CH 2 —, —COO—, —OCO—, —CF 2 O—, —COO—, —OCO—, —
  • R 1 preferably represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a linear or branched alkyl group having 1 to 12 carbon atoms in which one —CH 2 — or two or more unadjacent —CH 2 — may be each independently substituted by —O—, —COO—, —OCO—, or —O—CO—O—, or a group represented by —(X R —S R ) kR —P R , more preferably represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a linear alkyl group or linear alkoxy group having 1 to 12 carbon atoms, or a group represented by —(X R —S R ) kR —P R , and particularly preferably represents a group represented by —(X R —S R ) kR —P
  • P R represents a polymerizable group
  • S R represents a spacer group or a single bond, and when a plurality of S R are present, they may be the same or different
  • X R represents —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH ⁇ CH—COO—, —CH ⁇ CH—OCO—, —COO—CH ⁇ CH—, —OCO—CH ⁇ CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2
  • M 1 represents a divalent hydrocarbon group containing a conjugated system, and from the viewpoint of difficulty in occurrence of retardation decrease and discoloration, the total number of ⁇ electrons contained in M 1 is preferably 4to 50 and more preferably 4 to 24. From the viewpoint of liquid crystallinity, easy availability of raw materials, and easy synthesis, M 1 preferably represents a group represented by formula (I-M) below,
  • T represents a trivalent hydrocarbon group
  • B 1 represents a hydrogen atom, a methyl group, a methylidene group, or a cyclic hydrocarbon group, which may be unsubstituted or substituted by one or more L B
  • B 2 represents a single bond, a double bond, or a divalent cyclic hydrocarbon group, which may be unsubstituted or substituted by one or more L B
  • L B represents a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group,
  • T preferably represents a group selected from formula (T-1) to formula (T-22) below,
  • a bond may be present at any desired position, any desired —CH ⁇ may be each independently replaced by —N ⁇ , —CH 2 — may be each independently substituted by —O—, —S—, —NR 0 — (wherein R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS—, or —CO— without containing a —O—O— bond;
  • R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms
  • —CS— —CS—
  • —CO— without containing a —O—O— bond
  • the expression “a bond may be present at any desired position” represents that, for example, when T is a trivalent group, three bonds are present at any desired positions (this is true for the later expression “a bond may be present at any desired position” in the present invention), and these groups may be unsubstituted or substituted by one or more L T ;
  • L T represents a fluor
  • T represents a group selected from the formula (T-4), more specifically, T preferably represents a group represented by formula (T-4-1) or formula (T-4-2) below,
  • T represents a group selected from the formula (T-7), more specifically, T preferably represents a group selected from formula (T-7-1) to formula (T-7-21) below,
  • R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms
  • T represents a group selected from the formula (T-8)
  • T preferably represents a group selected from formula (T-8-1) to formula (T-8-16) below,
  • R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms
  • T represents a group selected from the formula (T-11)
  • T preferably represents a group selected from formula (T-11-1) to formula (T-11-4) below,
  • B 1 represents a hydrogen atom or a methyl group, a methylidene group, or a cyclic hydrocarbon group, which may be unsubstituted or substituted by one or more L B ; and from the viewpoint of liquid crystallinity, easy availability of raw materials, and easy synthesis, B 1 preferably represents a hydrogen atom or a methyl group or a methylidene group, which may be unsubstituted or substituted by one or more L B , or a group selected from formula (B-1-1) to formula (B-1-21) bellow,
  • a ring structure may have a bond at any desired position, any desired —CH ⁇ may be each independently replaced by —N ⁇ , —CH 2 — may be each independently substituted by —O—, —S—, —NR 0 — (wherein R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS—, or —CO— without containing a —O—O— bond, and these groups may be unsubstituted or substituted by one or more substituents L B ; B 1 more preferably represents a hydrogen atom, a methyl group which may be unsubstituted or substituted by one or more L B , a methylidene group which may be unsubstituted or substituted by one or more L B , or a group which may be unsubstituted or substituted by one or more L B and are selected from the formula (B-1-3), the formula (B-1-4), the formula (B-1-8),
  • a group represented by the formula (B-1-3) preferably represents a group selected from formula (B-1-3-1) to formula (B-1-3-7) below,
  • a ring structure may have a bond at any position
  • R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, and these groups may be unsubstituted or substituted by one or more substituents L B ).
  • a group represented by the formula (B-1-4) preferably represents a group selected from formula (B-1-4-1) to formula (B-1-4-8) below,
  • a ring structure may have a bond at any position, and these groups may be unsubstituted or substituted by one or more substituents L B ).
  • a group represented by the formula (B-1-5) preferably represents a group selected from formula (B-1-5-1) to formula (B-1-5-6) below,
  • a ring structure may have a bond at any position
  • R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, and these groups may be unsubstituted or substituted by one or more substituents L B ).
  • a group represented by the formula (B-1-6) preferably represents a group selected from formula (B-1-6-1) to formula (B-1-6-9) below,
  • a ring structure may have a bond at any position
  • R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, and these groups may be unsubstituted or substituted by one or more substituents L B ).
  • a group represented by the formula (B-1-7) preferably represents a group selected from formula (B-1-7-1) to formula (B-1-7-12) below,
  • a ring structure may have a bond at any position
  • R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, and these groups may be unsubstituted or substituted by one or more substituents L B ).
  • a group represented by the formula (B-1-8) preferably represents a group selected from formula (B-1-8-1) to formula (B-1-8-8) below,
  • a ring structure may have a bond at any position
  • R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, and these groups may be unsubstituted or substituted by one or more substituents L B
  • the group more preferably represents a group selected from the formula (B-1-8-6), the formula (B-1-8-7), and the formula (B-1-8-8).
  • a group represented by the formula (B-1-10) preferably represents a group selected from formula (B-1-10-1) to formula (B-1-10-19) below,
  • a ring structure may have a bond at any position
  • R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, and these groups may be unsubstituted or substituted by one or more substituents L B
  • the group more preferably represents a group selected from the formula (B-1-10-1), the formula (B-1-10-2), and the formula (B-1-10-3).
  • a group represented by the formula (B-1-11) preferably represents a group selected from formula (B-1-11-1) to formula (B-1-11-7) below,
  • a ring structure may have a bond at any position
  • R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, and these groups may be unsubstituted or substituted by one or more substituents L B ).
  • a group represented by the formula (B-1-12) preferably represents a group selected from formula (B-1-12-1) to formula (B-1-12-4) below,
  • a ring structure may have a bond at any position
  • R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, and these groups may be unsubstituted or substituted by one or more substituents L B ).
  • a group represented by the formula (B-1-13) preferably represents a group selected from formula (B-1-13-1) to formula (B-1-13-10) below,
  • a ring structure may have a bond at any position
  • R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, and these groups may be unsubstituted or substituted by one or more substituents L B ).
  • a group represented by the formula (B-1-17) preferably represents a group selected from formula (B-1-17-1) to formula (B-1-17-16) below,
  • a ring structure may have a bond at any position
  • R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, and these groups may be unsubstituted or substituted by one or more substituents L B ).
  • a group represented by the formula (B-1-18) preferably represents a group selected from formula (B-1-18-1) to formula (B-1-18-4) below,
  • a ring structure may have a bond at any position
  • R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, and these groups may be unsubstituted or substituted by one or more substituents L B ).
  • a group represented by the formula (B-1-19) preferably represents a group selected from formula (B-1-19-1) to formula (B-1-19-16) below,
  • a ring structure may have a bond at any position
  • R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, and these groups may be unsubstituted or substituted by one or more substituents L B ).
  • a group represented by the formula (B-1-20) preferably represents a group selected from formula (B-1-20-1) to formula (B-1-20-12) below,
  • a ring structure may have a bond at any position
  • R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, and these groups may be unsubstituted or substituted by one or more substituents L B ).
  • a group represented by the formula (B-1-21) preferably represents a group selected from formula (B-1-21-1) to formula (B-1-21-13) below,
  • a ring structure may have a bond at any position
  • R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, and these groups may be unsubstituted or substituted by one or more substituents L B ).
  • B 2 represents a single bond, a double bond, or a divalent cyclic hydrocarbon group which may be unsubstituted or substituted by one or more L B , and from the viewpoint of liquid crystallinity, easy availability of raw materials and easy synthesis, B 2 preferably represents a single bond, a double bond, or a group selected from formula (B-2-1) to formula (B-2-21) below,
  • a ring structure may have a bond at any desired position, any desired —CH ⁇ may be each independently replaced by —N ⁇ , —CH 2 — may be each independently substituted by —O—, —S—, —NR 0 — (wherein R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS—, or —CO— without containing a —O—O— bond, and these groups may be unsubstituted or substituted by one or more substituents L B ), and B 2 more preferably represents a single bond, a double bond, or a group selected from formula the formula (B-2-3) and the formula (B-2-4).
  • V 1 and V 2 each represent a single bond, a double bond, or a divalent bonding group, and from the viewpoint of liquid crystallinity, easy availability of raw materials, and easy synthesis, V 1 and V 2 preferably each represent a single bond, a double bond, or a group selected from formula (V-1) to formula (V-15) below,
  • Y 1 represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or a linear or branched alkyl group having 1 to 20 carbon atoms in which one —CH 2 — or two or more unadjacent —CH 2 — may be each independently substituted by —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —
  • n represents an integer of 0 to 10
  • n preferably represents an integer of 0 to 5 and more preferably represents 0, 1, 2, or 3.
  • L preferably represents a fluorine atom, a chlorine atom, a pentafluorosulfuranyl group, a nitro group, a cyano group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, or a linear or branched alkyl group having 1 to 20 carbon atoms in which any hydrogen atom may be substituted by a fluorine atom, and one —CH 2 — or two or more unadjacent —CH 2 — may be each independently substituted by a group selected from —O—, —S—, —CO—, —COO—, —OCO—, —O—CO—O—, —CH ⁇ CH—, —CF ⁇ CF—, and —C ⁇ C—, and more preferably represents a fluorine atom, a cyan
  • L B preferably represents a fluorine atom, a chlorine atom, a nitro group, a cyano group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, or a linear or branched alkyl group having 1 to 20 carbon atoms in which any hydrogen atom may be substituted by a fluorine atom, and one —CH 2 — or two or more unadjacent —CH 2 — may be each independently substituted by —O—, —S—, —CO—, —COO—, —OCO—, —O—CO—O—, —CH ⁇ CH—, —CF ⁇ CF—, or —C ⁇ C—, preferably represents a fluorine atom, a chlorine atom, a nitro group, a cyano group, a methyla fluorine atom, a chlorine atom, a nitro group, a
  • L T represents a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or a linear or branched alkyl group having 1 to 20 carbon atoms in which one —CH 2 — or two or more unadjacent —CH 2 — may be each independently substituted by —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O
  • L T preferably represents a fluorine atom, a chlorine atom, a nitro group, a cyano group, a methylamino group, a dimethylamino group, or a linear or branched alkyl group having 1 to 20 carbon atoms in which any hydrogen atom in the group may be substituted by a fluorine atom, and one —CH 2 — or two or more unadjacent —CH 2 — may be each independently substituted by —O—, —S—, —CO—, —COO—, —OCO—, —O—CO—O—, —CH ⁇ CH—, —CF ⁇ CF—, or —C ⁇ C—, preferably represents a fluorine atom, a chlorine atom, a nitro group, a cyano group, a methylamino group, a dimethylamino group, a diethyla
  • k represents an integer of 0 to 8
  • k preferably represents an integer of 0 to 4, more preferably represents an integer of 0 to 2, even more preferably represents 0 or 1, and particularly preferably represents 1.
  • m1 and m2 each independently represent an integer of 0 to 5, and m1+m2 represents an integer of 1 to 5.
  • m1 and m2 preferably each independently represent an integer of 1 to 4, more preferably represent an integer of 1 to 3, and particularly preferably represent 1 or 2.
  • m1+m2 preferably represents an integer of 1 to 4, more preferably represents 2, 3, or 4, and particularly preferably represent 2 or 4.
  • Preferred examples of the compound represented by the general formula (I) include compounds represented by formula (I-1) to formula (I-10) below.
  • the compound, of the present invention is preferably used for a nematic liquid crystal composition, a smectic liquid crystal composition, a chiral smectic liquid crystal composition, and a cholesteric liquid crystal composition.
  • a compound other than the compound of the present invention may be added to a liquid crystal composition using the reactive compound of the present invention.
  • Preferred examples of the other polymerizable compound used by being mixed with the polymerizable compound of the present invention include compounds represented by general formula (X-11) and/or
  • P 11 , P 12 , and P 13 each independently represent a polymerizable group
  • S 11 , S 12 , and S 13 each independently represent a single bond or an alkylene group having 1 to 20 carbon atoms, in which one —CH 2 — or two or more unadjacent —CH 2 — may be each independently substituted by —O—, —COO—, —OCO—, or —OCOO—
  • X 1 , X 2 , and X 3 each independently represent —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —
  • W 11 and W 12 each independently represent a hydrogen atom or a methyl group
  • S 14 and S 15 each independently represent an alkylene group having 2 to 18 carbon atoms
  • X 14 and X 15 each independently represent —O—, —COO—, —OCO—, or a single bond
  • Z 13 and Z 14 each independently represent —COO— or —OCO—
  • a 15 , A 16 , and A 17 each independently represent a 1,4-phenylene group which may be unsubstituted or substituted by a fluorine atom, a chlorine atom, a linear or branched alkyl group having 1 to 4 carbon atoms, or a linear or branched alkoxy group having 1 to 4 carbon atoms)
  • difunctional polymerizable compound examples include compounds represented by general formula (X-11b-1) to formula (X-11b-3) below
  • W 13 and W 14 each independently represent a hydrogen atom or a methyl group
  • S 16 and S 17 each independently represent an alkylene group having 2 to 18 carbon atoms.
  • compounds in which S 16 and S 17 each independently represent an alkylene group having 2 to 8 carbon atoms are particularly preferred.
  • Examples of a compound represented by the general formula (X-12) include compounds represented by general formula (X-12-1) to formula (X-12-7) below,
  • P 14 represents a polymerizable group
  • S 18 represents a single bond or an alkylene group having 1 to 20 carbon atoms, in which one —CH 2 — or two or more unadjacent —CH 2 — may be each independently substituted by —O—, —COO—, —OCO—, or —O—CO—O—
  • X 16 represents a single bond, —O—, —COO—, or —OCO—
  • Z 15 represents a single bond, —COO—, or —OCO—
  • L 11 represents a fluorine atom, a chlorine atom, or a linear or branched alkyl group having 1 to 10 carbon atoms in which one —CH 2 — or two or more unadjacent —CH 2 — may be each independently substituted by —O—, —COO—, or —OCO—
  • s11 represents an integer of 0 to 4
  • R 12 represents a hydrogen atom, a flu
  • a polymerizable compound without showing liquid crystallinity can be added to the polymerizable liquid crystal composition containing the compound of the present invention in a degree that does not significantly impair the liquid crystallinity of the composition.
  • any compounds recognized as polymer-forming monomers or polymer-forming oligomers in this technical field can be used without particular limitation. Examples thereof include compounds described in “Photocuring Technology Data Book, Materials (monomers, oligomers, and photopolymerization initiators)” (supervised by Kunihiro Ichimura and Kiyomi Kato, Technonet).
  • the compound of the present invention can be polymerized without using a photopolymerization initiator, but a photopolymerization initiator may be added according to purpose.
  • concentration of the photopolymerization initiator is preferably 0.1% to 15% by mass, more preferably 0.2% to 10% by mass, and even more preferably 0.4% to 8% by mass relative to the compound of the present invention.
  • the photopolymerization initiator include benzoin ethers, benzophenones, acetophenones, benzyl ketals, acylphosphine oxides, and the like.
  • the photopolymerization initiator examples include 2-methyl-1-(4-methylthiophenyl)-2-morpholinopropan-1-one (IRGACURE 907), benzoic acid [1-[4-(phenylthio)benzoyl]heptylidene]amino ester (IRGACURE OXE 01), and the like.
  • a thermopolymerization initiator examples include azo compounds, peroxides, and the like.
  • Specific examples of the thermopolymerization initiator include 2,2′-azobis(4-methoxy-2,4-dimethylvaleronitrile), 2,2′-azobis(isobutyronitrile), and the like.
  • one polymerization initiator may be used, or two or more polymerization initiators may be used in combination.
  • a stabilizer can be added to the liquid crystal composition of the present invention.
  • the stability which can be used include hydroquinones, hydroquinone monoalkyl ethers, tertiary butylcatechols, pyrogallols, thiophenols, nitro compounds, ⁇ -naphthylamines, ⁇ -naphthols, nitroso compounds, and the like.
  • the adding amount is preferably within a range of 0.005% by mass to 1% by mass, more preferably 0.02% by mass to 0.8% by mass, and even more preferably 0.03% by mass to 0.5% by mass relative to the composition.
  • one stabilizer may be used or two or more stabilizers may be used in combination.
  • Preferred examples of the stabilizer include compounds represented by formula (X-13-1) to formula (X-13-35),
  • n represents an integer of 0 to 20.
  • the polymerizable liquid crystal composition containing the compound of the present invention when used for applications such as films, optical elements, functional pigments, medical products, cosmetics, coating agents, synthetic resins, etc., a metal, a metal complex, a dye, a pigment, a colorant, a fluorescent material, a phosphorescent material, a surfactant, a leveling agent, a thixotropic agent, a gelation agent, a polysaccharide, an ultraviolet absorber, an infrared absorber, an antioxidant, an ion exchange resin, a metal oxide such as titanium oxide or the like, etc. can be added according to purposes.
  • a polymer produced by polymerizing the polymerizable liquid crystal composition containing the compound of the present invention can be used for various applications.
  • a polymer produced by polymerizing, without alignment, the polymerizable liquid crystal composition containing the compound of the present invention can be used as a light scattering plate, a depolarizing plate, or a moire fringe prevention plate.
  • a polymer produced by polymerization after alignment has optical anisotropy and is thus useful.
  • An optically anisotropic body can be produced by, for example, supporting the polymerizable liquid crystal composition containing the compound of the present invention on a substrate rubbed with a cloth or the like, a substrate having an organic thin film formed thereon, or a substrate having an alignment film formed by oblique vapor deposition of SiO 2 or holding the polymerizable liquid crystal composition between substrates and then polymerizing the polymerizable liquid crystal composition.
  • Examples of a method for supporting the polymerizable liquid crystal composition on the substrate include spin coating, die coating, extrusion coating, roll coating, wire bar coating, gravure coating, spray coating, dipping, printing, and the like.
  • an organic solvent may be added to the polymerizable liquid crystal composition.
  • the organic solvent include a hydrocarbon solvent, a halogenated hydrocarbon solvent, an ether solvent, an alcohol solvent, a ketone solvent, an ester solvent, an aprotic solvent, and the like.
  • hydrocarbon solvent examples include toluene and hexane; examples of the halogenated hydrocarbon solvent include methylene chloride; examples of the ether solvent include tetrahydrofuran, acetoxy-2-ethoxyethane propylene glycol monomethyl ether acetate; examples of the alcohol solvent include methanol, ethanol, and isopropyl alcohol; examples of the ketone solvent include acetone, methyl ethyl ketone, cyclohexanone, ⁇ -butyrolactone, N-methyl pyrrolidinone; examples of the ester solvent include ethyl acetate and cellosolve; and examples of the aprotic solvent include dimethyl formamide and acetonitrile.
  • the organic solvent may be properly selected in consideration of vapor pressure and solubility of the polymerizable liquid crystal composition.
  • natural drying, heat drying, reduced-pressure drying, or reduced-pressure heat drying can be used as a method for evaporating the organic solvent added.
  • it is effective to provide an intermediate layer such as a polyimide thin film or the like on the substrate or to add a leveling agent to the polymerizable liquid crystal material.
  • the method of providing an intermediate layer such as a polyimide thin film or the like on the substrate is effective for improving adhesion between the substrate and the polymer produced by polymerizing the polymerizable liquid crystal material.
  • the substrate may have a shape having a curved surface as a constituent part. Both an organic material and an inorganic material can be used as the material constituting the substrate.
  • organic material used as the material of the substrate examples include polyethylene terephthalate, polycarbonate, polyimide, polyamide, polymethyl methacrylate, polystyrene, polyvinyl chloride, polytetrafluoroethylene, polychlorotrifluoroethylene, polyarylate, polysulfone, triacetyl cellulose, cellulose, polyether ether ketone, and the like, and examples of the inorganic material include silicon, glass, calcite, and the like.
  • a method of polymerization by irradiation with active energy rays such as ultraviolet light or electron beams, or the like is preferred because the polymerization is desired to rapidly proceed.
  • active energy rays such as ultraviolet light or electron beams, or the like
  • ultraviolet light either a polarized light source or an unpolarized light source may be used.
  • the liquid crystal composition is polymerized in a state of being held between two substrates, at least the substrate on the irradiation surface side is required to have proper transparency to active energy rays.
  • Another method may also be used, which includes, after polymerization of only a specified portion using a mask during irradiation, changing the alignment state of an unpolymerized portion by changing a condition such as an electric field, a magnetic field, a temperature, or the like and further performing polymerization by irradiation with active energy rays.
  • the temperature during irradiation is preferably within a temperature range in which the liquid crystal state of the polymerizable liquid crystal composition of the present invention is maintained.
  • the polymerization is preferably performed at a temperature as close to room temperature as possible, that is, typically a temperature of 25° C., in view of avoiding induction of undesired therraopolymerization.
  • the intensity of active energy rays is preferably 0.1 mW/cm 2 to 2 W/cm 2 .
  • the intensity of 0.1 mW/cm 2 or less requires much time for completing photopolymerization and thus causes deterioration in productivity, while the intensity of 2 W/cm 2 or more causes the danger of degrading the polymerizable liquid crystal compound or the polymerizable liquid crystal composition.
  • the optically anisotropic body produced by polymerization can be subjected to heat treatment for the purpose of decreasing changes in the initial characteristics and attempting to exhibit stable characteristics.
  • the temperature of heat treatment is preferably within a range of 50° C. to 250° C., and time of heat treatment is preferably within 30 seconds to 12 hours.
  • optically anisotropic body produced by the method described above may be used as a single body separated from the substrate or used without being separated from the substrate. Also, the resultant optically anisotropic body may be used by stacking or by laminating on another substrate.
  • % represents “% by mass”.
  • an operation is preferably performed in inert gas such as nitrogen gas, argon gas, or the like.
  • Usual post-treatment is an operation for obtaining an intended compound from a reaction solution and represents an operation generally performed by a person skilled in the art, such as separation, extraction, neutralization, washing, drying, concentration, or the like.
  • a compound represented by the formula (I-1-1) was produced by the method described in Journal of Medicinal Chemistry, 2009, Vol. 52, No. 9, pp. 2989-3000.
  • the compound represented by the formula (I-1-1), triethylamine, and ethyl acetate were added to a reactor.
  • an ethyl acetate solution of thiophosgene was added dropwise and stirred under ice cooling.
  • the reaction solution was poured into water, and purification was performed by column chromatography after usual post-treatment.
  • the resultant compound was dissolved in 2-propanol, and the resultant solution was added dropwise to a reactor to which hydrazine monohydrate and 2-propanol had been added, followed by stirring.
  • the precipitate was filtered off and dried to produce a compound represented by the formula (I-1-2).
  • the compound represented by the formula (I-1-4) and dichloromethane were added to a reactor. Then, the resultant mixture was cooled to ⁇ 78° C. and boron tribromide was added and stirred. The reaction solution was poured into water, and purification was performed by column chromatography and recrystallization after usual post-treatment, thereby producing a compound represented by the formula (I-1-5).
  • a compound represented by the formula (I-1-8) was produced by the method described in Synthesis, 2010, No. 15, pp. 2616-2620.
  • the compound represented by the formula (I-1-8) and tetrahydrofuran were added to a reactor. Then, a hexane solution of butyllithium was added dropwise and stirred under cooling to ⁇ 78° C.
  • a tetrahydrofuran solution of the compound represented by the formula (I-1-7) was added dropwise and then the resultant mixture was stirred at room temperature.
  • the reaction solution was poured into an aqueous ammonium chloride solution, and purification was performed by column chromatography after usual post-treatment.
  • the resultant compound, acetonitrile, and 6M hydrochloric acid were added to a reactor and heated under stirring.
  • the reaction solution was poured into water, and purification was performed by column chromatography after usual post-treatment, thereby producing a compound represented by the formula (I-1-9).
  • the compound represented by the formula (I-1-9), 5% palladium carbon, and ethanol were added to a reactor and stirred under a hydrogen pressure of 0.5 MPa.
  • the palladium carbon was filtered off, and the solvent was distilled off to produce a compound represented by the formula (I-1-10).
  • the compound represented by the formula (I-1-10) and dichloromethane were added to a reactor. Then, the resultant mixture was cooled to ⁇ 78° C. and boron tribromide was added and stirred. The reaction solution was poured into water, and purification was performed by column chromatography and recrystallization after usual post-treatment, thereby producing a compound represented by the formula (I-1-11).
  • the compound represented by the formula (I-1-12), the compound represented by the formula (I-1-5), N,N-dimethylaminopyridine, and dichloromethane were added to a reactor. Then, diisopropyl carbodiimide was added dropwise and stirred under ice cooling. Then, purification was performed by column chromatography after usual post-treatment, thereby producing a compound represented by the formula (I-1-13).
  • a compound represented by the formula (I-1-14) was produced by the method described in Publication No. WO2009-116657A1.
  • the compound represented by the formula (I-1-13), the compound represented by the formula (I-1-14), N,N-dimethylaminopyridine, and dichloromethane were added to a reactor.
  • diisopropyl carbodiimide was added dropwise and stirred under ice cooling.
  • purification was performed by column chromatography and recrystallization after usual post-treatment, thereby producing a compound represented by the formula (I-1).
  • a compound represented by the formula (I-2-1), potassium thiocyanate, and acetic acid were added to a reactor. Then, bromine was added dropwise and stirred under ice cooling. Then, the precipitate was filtered off and dried. The resultant solid was dissolved in hot water, and an aqueous ammonia solution was added to the resultant-solution, followed by stirring. The solid was filtered off and purification was performed by column chromatography and recrystallization to produce a compound represented by the formula (I-2-2).
  • the compound represented by the formula (I-2-2), p-toluenesulfonic acid monohydrate, and acetonitrile were added to a reactor. Then, an aqueous sodium nitride solution and an aqueous potassium iodide solution were added dropwise under ice cooling and stirred at room temperature. Then, purification was performed by column chromatography after usual post-treatment, thereby producing a compound represented by the formula (I-2-3).
  • the compound represented by the formula (I-2-4), potassium carbonate, and methanol were added to a reactor and stirred. Then, purification was performed by column chromatography after usual post-treatment, thereby producing a compound represented by the formula (I-2-5).
  • the compound represented by the formula (I-2-5), a compound represented by the formula (I-2-6), copper(I) iodide, tetrakis(triphenylphosphine) palladium(0), triethylamine, and N,N-dimethylformamide were added to a reactor and heated and stirred. Then, purification was performed by column chromatography after usual post-treatment, thereby producing a compound represented by the formula (I-2-7).
  • the compound represented by the formula (I-2-7) and dichloromethane were added to a reactor. Then, boron tribromide was added dropwise and stirred at ⁇ 78° C. The reaction solution was poured into water, and purification was performed by column chromatography after usual post-treatment, thereby producing a compound represented by the formula (I-2-8).
  • a compound represented by the formula (I-2-9), ethylene glycol, triphenylphosphine, and tetrahydrofuran were added to a reactor. Then, diisopropyl azodicarboxylate was added dropwise and stirred. Then, purification was performed by column chromatography after usual post-treatment, thereby producing a compound represented by the formula (I-2-10).
  • the compound represented by the formula (I-2-10), rhodium, and diisopropyl alcohol were added to a reactor and heated and stirred under a hydrogen pressure of 5 atm.
  • the catalyst was removed, and then purification was performed by column chromatography, thereby producing a compound represented by the formula (I-2-11).
  • the compound represented by the formula (I-2-12), methanol, and an aqueous sodium hydroxide solution were added to a reactor. Then, the resultant mixture was neutralized with hydrochloric acid, and purification was performed by column chromatography after usual post-treatment, thereby producing a compound represented by the formula (I-2-13).
  • the compound represented by the formula (I-2-13), the compound represented by the formula (I-2-8), N,N-dimethylaminopyridine, and dichloromethane were added to a reactor. Then, diisopropyl carbodiimide was added dropwise and stirred. Then, purification was performed by column chromatography after usual post-treatment, thereby producing a compound represented by the formula (I-2-14).
  • a compound represented by the formula (I-2-16) was produced by the method described in Synthesis, 2001, No. 10, pp. 1519-1522.
  • the compound represented by the formula (I-2-15), the compound represented by the formula (I-2-16), triphenylphosphine, and tetrahydrofuran were added to a reactor.
  • diisopropyl azodicarboxylate was added dropwise and stirred.
  • purification was performed by column chromatography after usual post-treatment, thereby producing a compound represented by the formula (I-2-17).
  • the compound represented by the formula (I-2-17), methanol, and an aqueous sodium hydroxide solution were added to a reactor. Then, the resultant mixture was neutralized with hydrochloric acid, and purification was performed by column chromatography after usual post-treatment, thereby producing a compound represented by the formula (I-2-18).
  • a compound represented by the formula (I-3-1), concentrated sulfuric acid, and ethanol were added to a reactor and heated under reflux. Then, the resultant mixture was diluted with ethyl acetate, and purification was performed by column chromatography after usual post-treatment, thereby producing a compound represented by the formula (I-3-2).
  • a compound represented by the formula (I-3-3) was produced by the method described in Tetrahedron Letters, 2010, Vol. 51, No. 17, pp. 2323-2325.
  • the compound represented by the formula (I-3-2), the compound represented by the formula (I-3-3), dibutyltin oxide, and toluene were added to a reactor and heated under reflux while the solvent was replaced. Then, purification was performed by column chromatography after usual post-treatment to produce a compound represented by the formula (I-3-4).
  • the compound represented by the formula (I-4-2), sodium dihydrogen phosphate dihydrate, methanol, water, and an aqueous hydrogen peroxide solution were added to a reactor. Then, an aqueous sodium chlorite solution was added dropwise and heated and stirred. The resultant mixture was cooled by adding water, and the precipitate was filtered off and dried to produce a compound represented by the formula (I-4-4).
  • the compound represented by the formula (I-4-4), trimethylsilyl acetylene, copper(I) iodide, triethylamine, and N,N-dimethylformamide were added to a reactor and heated and stirred. Then, purification was performed by column chromatography after usual post-treatment to produce a compound represented by the formula (I-4-5).
  • the compound represented by the formula (I-4-10) and dichloromethane were added to a reactor.
  • the resultant mixture was cooled, and bromine was added dropwise and stirred.
  • the reaction solution was poured into water, and then purification was performed by column chromatography after usual post-treatment to produce a compound represented by the formula (I-4-11).
  • the compound represented by the formula (I-4-11) and dichloromethane were added to a reactor.
  • the resultant mixture was cooled to ⁇ 78° C., and boron tribromide was added dropwise and stirred.
  • the reaction solution was poured into water, and then purification was performed by column chromatography after usual post-treatment to produce a compound represented by the formula (I-4-12).
  • the compound represented by the formula (I-4-12), a compound represented by the formula (I-4-13), potassium acetate, bis(triphenylphosphine) palladium(II) dichloride, and dimethylsulfoxide were added to a reactor and heated and stirred. Then, purification was performed by column chromatography after usual post-treatment to produce a compound represented by the formula (I-4-14).
  • the compound represented by the formula (I-4-14), a compound represented by the formula (I-4-15), potassium carbonate, tetrakis(triphenylphosphine)palladium(0), ethanol, and water were added to a reactor and heated under reflux. Then, purification was performed by column chromatography after usual post-treatment to produce a compound represented by the formula (I-4-16).
  • the compound represented by the formula (I-4-16), the compound represented by the formula (I-4-6), copper(I) iodide, triethylamine, N,N-dimethylformamide, and tetrakis(triphenylphosphine)palladium(0) were added to a reactor and heated and stirred. Then, purification was performed by column chromatography after usual post-treatment to produce a compound represented by the formula (I-4-17).
  • a compound represented by the formula (I-4-19) was produced by the method described in Publication No. WO993770A1.
  • the compound represented by the formula (I-4-18), the compound represented by the formula (I-4-19), N,N-dimethylaminopyridine, and dichloromethane were added to a reactor.
  • diisopropyl carbodiimide was added dropwise and stirred.
  • purification was performed by column chromatography and recrystallization after usual post-treatment to produce a compound represented by the formula (I-4).
  • a compound represented by the formula (I-5-1), 3-chloropropyl acrylate, cesium carbonate, and dimethylsuifoxide were added to a reactor and heated and stirred. Then, purification was performed by column chromatography after usual post-treatment to produce a compound represented by the formula (I-5-2).
  • a compound represented by the formula (I-5-3), a compound represented by the formula (I-5-4), potassium carbonate, ethanol, and tetrakis(triphenylphosphine) palladium(0) were added to a reactor and heated under reflux. Then, purification was performed by column chromatography after usual post-treatment to produce a compound represented by the formula (I-5-5).
  • a compound represented by the formula (I-5-6), tert-butyl acrylate, potassium carbonate, and N,N-dimethylformamide, palladium(II) acetate were added to a reactor and heated and stirred. Then, purification was performed by column chromatography after usual post-treatment to produce a compound represented by the formula (I-5-7).
  • the compound represented by the formula (I-5-7), 5% palladium carbon, and tetrahydrofuran were added to a reactor and stirred under a hydrogen pressure of 0.5 MPa.
  • the catalyst was filtered off, and then purification was performed by column chromatography after usual post-treatment to produce a compound represented by the formula (I-5-8).
  • the compound represented by the formula (I-5-10), a compound represented by the formula (I-5-11), N,N-dimethylaminopyridine, and dichloromethane were added to a reactor. Then, diisopropyl carbodiimide was added dropwise and stirred. Then, purification was performed by column chromatography after usual post-treatment to produce a compound represented by the formula (I-5-12).
  • the compound represented by the formula (I-5-12) and dichloromethane were added to a reactor. Then, trifluoroacetic acid was added dropwise and stirred under ice cooling. Then, purification was performed by column chromatography after usual post-treatment to produce a compound represented by the formula (I-5-13).
  • the compound represented by the formula (I-5-13), the compound represented by the formula (I-5-2), N,N-dimethylaminopyridine, and dichloromethane were added to a reactor. Then, diisopropyl carbodiimide was added dropwise and stirred under ice cooling. Then, purification was performed by column chromatography and recrystallization after usual post-treatment to produce a compound represented by the formula (I-5).
  • a compound represented by the formula (I-6-1), toluene, ethyl propiolate, and dibutyltin oxide were added to a reactor and heated under reflux. Then, purification was performed by column chromatography after usual post-treatment to produce a compound represented by the formula (I-6-2).
  • a compound represented by the formula (I-6-3), 3-chloropropylamine, cesium carbonate, and dimethylsulfoxide were added to a reactor and heated and stirred. Then, purification was performed by column chromatography after usual post-treatment to produce a compound represented by the formula (I-6-4).
  • the compound represented by the formula (I-6-4), methanol, and an aqueous sodium hydroxide solution were added to a reactor and heated and stirred. Then, purification was performed by column chromatography and recrystallization after usual post-treatment to produce a compound represented by the formula (I-6-5).
  • the compound represented by the formula (I-6-5), acetic acid, and 5% rhodium carbon were added to a reactor and heated and stirred in a hydrogen atmosphere.
  • the catalyst was removed, and then purification was performed by column chromatography and recrystallization after usual post-treatment to produce a compound represented by the formula (I-6-6).
  • the compound represented by the formula (I-6-10), water, and methanol were added to a reactor. Then, in an inert atmosphere, an acetic acid-methanol solution of a compound represented by the formula (I-6-11) was added dropwise and stirred under cooling. Then, usual post-treatment was performed in an inert atmosphere to produce a compound represented by the formula (I-6-12).
  • a compound represented by the formula (I-7-1), pyridine, and dichloromethane were added to a reactor. Then, a dichloromethane solution of acetyl chloride was added dropwise and stirred under ice cooling. Then, purification was performed by column chromatography after usual post-treatment to produce a compound represented by the formula (I-7-2).
  • the compound represented by the formula (i-7-7), ethanol, and hydrazine monohydrate were added to a reactor.
  • the resultant mixture was diluted with dichloromethane, and then purification was performed by column chromatography after usual post-treatment to produce a compound represented by the formula (I-7-8).
  • the compound represented by the formula (I-7-8), a compound represented by the formula (I-7-9), and ethanol were added to a reactor and stirred.
  • the resultant mixture was diluted with dichloromethane, and then purification was performed by column chromatography after usual post-treatment to produce a compound represented by the formula (I-7-10).
  • a compound represented by the formula (I-7-12) was produced by the method described in Macromolecular Chemistry and Physics, 2009, Vol. 210, No. 7, pp. 531-541.
  • a compound represented by the formula (I-7-11), the compound represented by the formula (I-7-12), tetrahydrofuran, triphenylphosphine were added to a reactor.
  • diisopropyl azodicarboxylate was added dropwise and stirred under ice cooling.
  • purification was performed by column chromatography after usual post-treatment to produce a compound represented by the formula (I-7-13).
  • the compound represented by the formula (I-7-13), methanol, water, sodium dihydrogen phosphate dihydrate, sodium chlorite, and hydrogen peroxide were added to a reactor and heated and stirred. Then, water was added to the resultant mixture, and the precipitate was filtered off and dried to produce a compound represented by the formula (I-7-14).
  • the compound represented by the formula (I-7-14), a compound represented by the formula (I-7-15), N,N-dimethylaminopyridine, and dichloromethane were added to a reactor. Then, diisopropyl carbodiimide was added dropwise and stirred under ice cooling. Then, purification was performed by column chromatography after usual post-treatment to produce a compound represented by the formula (I-7-16).
  • the compound represented by the formula (I-7-16), methanol, and an aqueous sodium hydroxide solution were added to a reactor and heated and stirred. Then, purification was performed by column chromatography after usual post-treatment to produce a compound represented by the formula (I-7-17).
  • the compound represented by the formula (I-7-17), a compound represented by the formula (I-7-18), N,N-dimethylaminopyridine, and dichloromethane were added to a reactor. Then, diisopropyl carbodiimide was added dropwise and stirred under ice cooling. Then, purification was performed by column chromatography after usual post-treatment to produce a compound represented by the formula (I-7-19).
  • a compound represented by the formula (I-8-1), propiolic acid, 4-chlorobutanol, cesium carbonate, and dimethylsulfoxide were added to a reactor and heated and stirred. Then, purification was performed by column chromatography after usual post-treatment to produce a compound represented by the formula (I-8-2).
  • the compound represented by the formula (I-8-3), sodium dihydrogen phosphate dihydrate, methanol, water, sodium chlorite, and an aqueous hydrogen peroxide solution were added to a reactor and heated and stirred.
  • the resultant mixture was diluted with ethyl acetate, and then purification was performed by column chromatography after usual post-treatment to produce a compound represented by the formula (I-8-4).
  • the compound represented by the formula (I-8-5), sodium dihydrogen phosphate dihydrate, methanol, water, sodium chlorite, and an aqueous hydrogen peroxide solution were added to a reactor and heated and stirred.
  • the resultant mixture was diluted with ethyl acetate, and then purification was performed by column chromatography after usual post-treatment to produce a compound represented by the formula (I-8-6).
  • a compound represented by the formula (I-8-8), tetrahydrofuran, and sodium hydride were added to a reactor and stirred.
  • a tetrahydrofuran solution of the compound represented by the formula (I-8-7) was added dropwise and heated and stirred. Water was added to the mixture, and then purification was performed by column chromatography after usual post-treatment to produce a compound represented by the formula (I-8-9).
  • the compound represented by the formula (I-8-12), sodium dihydrogen phosphate dihydrate, methanol, water, sodium chlorite, and an aqueous hydrogen peroxide solution were added to a reactor and heated and stirred.
  • the resultant mixture was diluted with ethyl acetate, and then purification was performed by column chromatography after usual post-treatment to produce a compound represented by the formula (I-8-13).
  • a compound represented by the formula (I-8-14) was produced by the method described in European Journal of Organic Chemistry, 2004, No. 20, pp. 4203-4214.
  • the compound represented by the formula (I-8-14), water, and methanol were added to a reactor.
  • an acetic acid-methanol solution of a compound represented by the formula (I-8-15) was added dropwise and stirred under ice cooling.
  • post-treatment was performed to produce a compound represented by the formula (I-8-16).
  • the compound represented by the formula (I-8-17), the compound represented by the formula (I-8-13), N,N-dimethylaminopyridine, and dichloromethane were added to a reactor. Then, diisopropyl carbodiimide was added dropwise and stirred under ice cooling. Then, purification was performed by column chromatography and recrystallization after usual post-treatment to produce a compound represented by the formula (I-8-18).
  • a compound represented by the formula (I-9-2), acetonitrile, potassium carbonate, and a compound represented by the formula (I-9-1) were added to a reactor and heated and stirred. Then, purification was performed by column chromatography after usual post-treatment to produce a compound represented by the formula (I-9-3).
  • the compound represented by the formula (I-9-3), methanol, tin(II) chloride, and concentrated hydrochloric acid were added to a reactor and stirred.
  • the reaction solution was poured into an aqueous sodium bicarbonate solution, and then purification was performed by column chromatography after usual post-treatment to produce a compound represented by the formula (I-9-4).
  • a compound represented by the formula (I-9-6), methanol, and an aqueous sodium hydroxide solution were added to a reactor and heated and stirred. Then, purification was performed by column chromatography after usual post-treatment to produce a compound represented by the formula (I-9-7).
  • the compound represented by the formula (I-9-11), the compound represented by the formula (I-9-8), potassium carbonate, ethanol, and tetrakis(triphenylphosphine)palladium(0) were added to a reactor and heated and stirred. Then, purification was performed by column chromatography and recrystallization after usual post-treatment to produce a compound represented by the formula (I-9-12).
  • the compound represented by the formula (I-9-12), a compound represented by the formula (I-9-13), triphenylphosphine, and tetrahydrofuran were added to a reactor and heated. Then, diisopropyl azodicarboxylate was added and stirred under ice cooling. Then, purification was performed by column chromatography and recrystallization after usual post-treatment to produce a compound represented by the formula (I-9-14).
  • the compound represented by the formula (I-9-14) and dichloromethane were added to a reactor.
  • the resultant mixture was cooled to ⁇ 78° C., and boron tribromide was added dropwise and stirred.
  • the reaction solution was poured into water, and then purification was performed by column chromatography and recrystallization after usual post-treatment to produce a compound represented by the formula (I-9-15).
  • the compound represented by the formula (I-9-15), a compound represented by the formula (I-9-16), N,N-dimethylaminopyridine, and dichloromethane were added to a reactor. Then, diisopropyl carbodiimide was added dropwise and stirred under ice cooling. Then, purification was performed by column chromatography and recrystallization after usual post-treatment to produce a compound represented by the formula (I-9-17).
  • the compound represented by the formula (I-9-17) and dichloromethane were added to a reactor. Then, trifiuoroacetic acid was added and stirred under ice cooling. The reaction solution was poured into water, and then purification was performed by column chromatography and recrystallization after usual post-treatment to produce a compound represented by the formula (I-9-18).
  • a compound represented by the formula (I-9-19), a compound represented by the formula (I-9-20), N,N-dimethylaminopyridine, and dichloromethane were added to a reactor. Then, diisopropyl carbodiimide was added dropwise and stirred under ice cooling. Then, purification was performed by column chromatography after usual post-treatment to produce a compound represented by the formula (I-9-21).
  • the compound represented by the formula (I-9-21), the compound represented by the formula (I-9-18), N,N-dimethylaminopyridine, and dichloromethane were added to a reactor. Then, diisopropyl carbodiimide was added dropwise and stirred under ice cooling. Then, purification was performed by column chromatography and recrystallization after usual post-treatment to produce a compound represented by the formula (I-9).
  • a compound represented by the formula (I-10-1) and ethanol were added to a reactor. Then, hydrazine monohydrate was added dropwise and stirred. Then, purification was performed by column chromatography after usual post-treatment to produce a compound represented by the formula (I-10-2).
  • a compound represented by the formula (I-10-3) and ethanol were added to a reactor.
  • An ethanol solution of the compound represented by the formula (I-10-2) was added dropwise and stirred. Then, purification was performed by column chromatography after usual post-treatment to produce a compound represented by the formula (I-10-4).
  • the compound represented by the formula (I-10-8) and acetonitrile were added to a reactor. Then, trimethyl phosphite and sodium iodide were added and stirred. The solvent was distilled off, water was added, and then the resultant solid was filtered off and dried to produce a compound represented by the formula (I-10-9).
  • the compound represented by the formula (I-10-9) and tetrahydrofuran were added to a reactor.
  • the resultant mixture was cooled to ⁇ 78° C., and a hexane solution of butyl lithium was added dropwise and stirred.
  • a tetrahydrofuran solution of the compound represented by the formula (I-10-5) was added dropwise and stirred.
  • purification was performed by column chromatography and recrystallization after usual post-treatment to produce a compound represented by the formula (I-10-10).
  • the compound represented by the formula (I-10-10) and tetrahydrofuran were added to a reactor.
  • the resultant mixture was cooled to ⁇ 78° C., and a hexane solution of butyl lithium was added dropwise and stirred.
  • a tetrahydrofuran solution of ethylene oxide was added dropwise and stirred.
  • purification was performed by column chromatography and recrystallization after usual post-treatment to produce a compound represented by the formula (I-10-11).
  • the compound represented by the formula (I-10-11) and dichloromethane were added to a reactor.
  • the resultant mixture was cooled to ⁇ 78° C., and boron tribromide was added dropwise and stirred.
  • the reaction solution was poured into water, and then purification was performed by column chromatography and recrystallization after usual post-treatment to produce a compound represented by the formula (I-10-12).
  • the compound represented by the formula (I-10-12), a compound represented by the formula (I-10-13), dibutyltin oxide, and toluene were added to a reactor and heated and stirred. Then, purification was performed by column chromatography after usual post-treatment to produce a compound represented by the formula (I-10-14).
  • a compound represented by the formula (I-10-16), tetrahydrofuran, and sodium hydride were added to a reactor and stirred.
  • a tetrahydrofuran solution of the compound represented by the formula (I-10-15) was added dropwise and heated and stirred. Then, water was added dropwise, and purification was performed by column chromatography after usual post-treatment to produce a compound represented by the formula (I-10-17).
  • the compound represented by the formula (I-10-19), a compound represented by the formula (I-10-20), triphenylphosphine, and tetrahydrofuran were added to a reactor. Then, diisopropyl azodicarboxylate was added dropwise and stirred under ice cooling. Then, purification was performed by column chromatography after usual post-treatment to produce a compound represented by the formula (I-10-21).
  • the compound represented by the formula (I-10-21), sodium dihydrogen phosphate dihydrate, methanol, water, sodium hydrochlorite, and an aqueous hydrogen peroxide solution were added to a reactor and heated and stirred.
  • the reaction solution was diluted with ethyl acetate, and then purification was performed by column chromatography after usual post-treatment to produce a compound represented by the formula (I-10-22).
  • the compound represented by the formula (I-10-22), the compound represented by the formula (I-10-14), N,N-dimethylaminopyridine, and dichloromethane were added to a reactor. Then, diisopropyl carbodiimide was added dropwise and stirred under ice cooling. Then, purification was performed by column chromatography and recrystallization after usual post-treatment to produce a compound represented by the formula (I-10).
  • a polyimide solution for an alignment film was applied by a spin coating method on a glass substrate having a thickness of 0.7 mm, dried at 100° C. for 10 minutes, and then fired at 200° C. for 60 minutes to produce a coating film.
  • the resultant coating film was rubbed. Rubbing was performed by using a commercial rubbing apparatus.
  • a coating solution was prepared by adding 1% of photopolymerization initiator Irgacure 907 (manufactured by BASF Corporation), 0.1% of 4-methoxyphenol, and 80% of chloroform to a composition prepared by adding 30% of each of the compounds to be evaluated to the mother liquid crystal (X).
  • the resultant coating solution was applied to the rubbed glass substrate by a spin coating method.
  • the coating solution was dried at 80° C. for 1 minute and further dried at 120° C. for 1 minute.
  • the substrate was irradiated with ultraviolet light for 25 seconds by using a high-pressure mercury lamp with an intensity of 40 mW/cm 2 , thereby producing a film to be evaluated. Any of the resultant films was horizontally aligned.
  • a correspondence relation between the film to be evaluated and each of the used compounds to be evaluated is shown in a table below.
  • the resultant film to be evaluated was measured with respect to an absorption maximum wavelength ⁇ omax in an in-plane direction perpendicular to the alignment direction. Measurement was performed by using a spectrophotometer (V-560 manufactured by JASCO Corporation), and the film to be evaluated was held between two polarization plates and arranged so that the alignment direction of the film to be evaluated was perpendicular to the polarization direction of the polarization plates (refer to the drawing). Also, the film to be evaluated was arranged so that the alignment direction of the film to be evaluated was perpendicular to the polarization direction of the polarization plates, and absorbance Ao in the in-plane direction perpendicular to the alignment direction at the wavelength ⁇ omax was measured.
  • the film to be evaluated was arranged so that the alignment direction of the film to be evaluated was parallel to the polarization direction of the polarization plates, and absorbance Ae in the direction parallel to the alignment direction at the wavelength ⁇ omax was measured.
  • Ao/Ae was calculated from the obtained Ao and Ae. The results are shown in a table below.
  • Example Film to be evaluated Ao/Ae
  • Example 11 Optically anisotropic body (XI-1) 345 1.13
  • Example 12 Optically anisotropic body (XI-2) 365 1.01
  • Example 13 Optically anisotropic body (XI-3) 332 1.12
  • Example 14 Optically anisotropic body (XI-4) 378 1.11
  • Example 15 Optically anisotropic body (XI-5) 405 1.01
  • Example 16 Optically anisotropic body (XI-6) 320 1.02
  • Example 17 Optically anisotropic body (XI-7) 420 1.01
  • Example 18 Optically anisotropic body (XI-8) 321 0.88
  • Example 19 Optically anisotropic body (XI-9) 350 1.01
  • Example 20 Optically anisotropic body (XI-10) 418 1.05 Comparative Optically anisotropic body (XI-R-1) 315 1.02
  • retardation retention rate (%) Re (550) (after test)/Re (550) (before test)) ⁇ 100) of retardation Re (550) before and after a heat resistance/light resistance test of each of the films to be evaluated.
  • the retardation was measured by using an inspection apparatus (RETS-100 manufactured by Otsuka Electronics Co., Ltd.).
  • Yellowness (YI) was measured by using a spectrophotometer (V-560 manufactured by JASCO Corporation), and yellowness (YI) was calculated by using a color diagnosis program.
  • a calculation formula is the following.
  • Example 21 Optically anisotropic body (XII-1) 95% 0.4
  • Example 22 Optically anisotropic body (XII-2) 96% 0.3
  • Example 23 Optically anisotropic body (XII-3) 95% 0.4
  • Example 24 Optically anisotropic body (XII-4) 89% 0.7
  • Example 25 Optically anisotropic body (XII-5) 91% 0.6
  • Example 26 Optically anisotropic body (XII-6) 88% 0.8
  • Example 27 Optically anisotropic body (XII-7) 90% 0.7
  • Example 28 Optically anisotropic body (XII-8) 84% 1.2
  • Example 29 Optically anisotropic body (XII-9) 95% 0.4
  • Example 30 Optically anisotropic body (XII-10) 89% 0.7 Comparative Optically anisotropic body (XII-R-1) 70% 5.1
  • Example 3 Comparative Optically anisotropic body (X
  • the results described above indicate that the compounds represented by the formula (I-1) to the formula (I-10) of the present invention described in Example 1 to Example 10 cause little decrease in retardation and little discoloration. Therefore, the compounds of the present invention are useful as a component of a polymerizable composition. Also, an optically anisotropic body using a polymerizable liquid crystal composition containing each of the compounds of the present invention is useful for application to an optical film and the like.
  • FIG. 1 an arrangement of a film to be evaluated and a polarization plate, (a): a state in which the alignment direction of a film to be evaluated is parallel to the polarization direction of a polarization plate, (b): a state in which the alignment direction of a film to be evaluated is perpendicular to the polarization direction of a polarization plate, 1: polarization plate (an arrow represents the polarization direction of a polarization plate), 2: a film to be evaluated (an arrow represents the alignment direction), I 0 : incident light, I: transmitted light

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JP7251291B2 (ja) * 2019-04-23 2023-04-04 コニカミノルタ株式会社 光応答性高分子化合物
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